


I Could Fall In Love

by Miss_Tricksy



Category: Supernatural
Genre: F/M
Language: English
Status: In-Progress
Published: 2020-01-07
Updated: 2020-01-06
Packaged: 2021-02-27 09:14:12
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,666
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/22154599
Author URL: https://archiveofourown.org/users/Miss_Tricksy/pseuds/Miss_Tricksy
Summary: Just a chance encounter with the Winchesters for the first time in a long time.
Relationships: Dean Winchester & You, Sam Winchester & You





	I Could Fall In Love

**Author's Note:**

> This was originally posted on Tumblr for Yvette's Mystery Song Challenge. My song was I Could Fall in Love by Selena. I don't know how to do links, so if I figure that out I'll try to fix it.

You hadn’t seen Sam Winchester for almost 5 years. The last time you had stayed more than a day at your ‘uncle’ Bobby’s house. And he had just been starting to fill out a bit, 17 and starting to become too tall for his own good. Dimples for days and a smile you were honestly a little jealous of. When he walked in to the diner where you were having lunch, you could almost swear you felt the earth tilt just a little.  
He came in, eyes down cast, and plopped into a booth, and despite seeming aloof, you noticed him scanning every other patron in the place and the route to every exit. His brother trailed behind, heading straight to the bathroom. Dean had always been a bit of a germ-a-phobe and you knew he wouldn’t touch his burger without washing the road dust off first.  
Sam glanced through the menu in record time, which you knew wasn’t much of a feat considering the limited offerings at Mabel’s Place. You watched him glance his brother’s direction, eyes flickering your way for a couple seconds, then smiling at the matronly waitress. Both boys ordered lunch and you debated about saying hello.  
You knew Sam’s girlfriend had died in a suspicious fire not too very long ago, and that they were on the tail of something big. World ending, epically BIG. You weren’t sure if you were quite up for that kind of chaos in your life. You were in the process of getting out of hunting and into civilian life. The degree you had gotten in teaching had been a bit of a feat, and so far, the money you were making tutoring was more than enough to pay your rent and finance the odd ghoul hunt. Getting involved in the Winchester’s lives would only complicate things for you.  
You sipped your coffee and tore your brownie into chunks, avoiding meeting Sam’s gaze but still noticing him and Dean giving you more attention than most of the other patrons. The last time you had seen them you were barely 16. Your hair was much darker, your braces were still on, and you were a few pounds lighter. The teal rimmed glasses you were wearing made your eyes stand out like crazy and the make-up you had on was unheard of when you had been kids. But it made you feel a little more confident going into the interview you had scheduled later that day.  
A wave of nostalgia washed over you, the longer you sat there. Your folks had grown up with Bobby Singer and you had known him your whole life. When his wife died, he got a little weird. Then some guy named John Winchester started showing up at the junkyard with two kids in tow. And Bobby got a little weirder. By the time you were 13 you understood why. Bobby was a Hunter of all things supernatural. You had thought all his strange books were a holdover from his abusive upbringing. When Bobby broke some ribs and a buddy of his was laid up with a whole host of nasty scratches down both legs, your mother had hounded you in to helping Bobby around the house. One day when you were vacuuming you found a particularly wicked looking dagger under the edge of a couch. When you questioned Bobby about it you forced him to tell you the truth about why it was covered in blood.  
The summer before your junior year of high school you got to know the Winchesters quite well, but Sam especially. You liked to hang out at Bobby’s and help him do research for his hunts and your parents were happy to know you were staying out of trouble. Sam spent quite a bit of his summer at Bobby’s that year too. He had broken a wrist from a bar fight in May, was recovering from a concussion most of June, and in August John dropped him off while he and Dean hunted werewolves in Canada.  
You had let your thoughts wander a bit too long because when you blinked back to reality, Sam Winchester was sitting across from you, one dimple exposed, and watercolor eyes staring at you.  
“Y/F/N Y/L/N, you really shouldn’t let strangers sneak up on you like that, you know.”  
“Not a stranger if I’ve known you half my life, and helped you change your brother’s bandages, dontcha think, Sam Winchester.”  
The smile that lit Sam’s face was the most beautiful thing you had seen in quite a while, both dimples making an appearance. “Guess you’re right about that,” he laughed. He glanced around the small restaurant before asking, “What are you doing in Wyoming?”  
Before you could answer Dean fell in to the bench beside you, arm automatically reaching behind you. “Y/N/N you are a sight for sore eyes. You living around here?”  
“I was just getting ready to tell your brother, before you so rudely interrupted, I’m on my way to a job interview. There’s a private school about 20 minutes up the road that’s hiring. They apparently have lost 4 or 5 staff members since school started.” You noticed Sam’s eyebrows disappear under his bangs. “One of the positions is basically teaching a folklore class to high schoolers. Thought it would be a good fit for me.” You glanced at Dean, but his gaze was locked with his brother and you could tell they were having one of their ‘private conversations’. “Okay, spit it o………….wait.” Your eyes bounced from freckles to dimples and back. “Is that why you guys are in town? I seriously picked a monster infested school?”  
Dean huffed at your description and shrugged his shoulders. “Sam seems to think something’s going on down at Bedford Academy.”  
“Dude,” Sam scoffed his brother’s way, “five teachers have gone missing, one was found and was extremely disoriented and swears she just went for a walk around the tennis courts, but was actually missing for 3 days. The school is trying to push for a new set of dormitories. This case is practically on a platter for us.”  
“And Sam is afraid Bobby’s going to kick his ass since he hasn’t seen him for oh, five years or so and he’s dragging his feet to get to Sioux Falls.”  
Sam glared at Dean, then softened his face when he looked at you. “That is only sort of true. I haven’t been to South Dakota. Bobby came to see me once in California.” His glance toward his brother screamed ‘bet you didn’t know that’. “And we kept in touch through e-mail. I actually think I helped him on one of Y/N’s cases. A weird lightshow in Oklahoma, think it was a bust,” he shrugged then turned a megawatt smile your way. “Anyhow, we should let you get going, I guess.”  
You couldn’t help but smile back, butterflies dancing in you stomach. “I’ve got some time. We should catch up a bit. You can fill me in on this case. Maybe I can get you some info when I do my interview. It wouldn’t be weird for me to ask for a tour of the grounds or find out what else is being kept out of the papers.” You flagged the waitress down for some coffee refills, smiling to yourself when Sam made a grumpy face when he realized you had used the last of the good creamer from your table. That smile quickly morphed in to a stifled moan when he leaned back to the booth behind him to grab a handful of the small containers, his abs and treasure trail on full display. You hoped the blush you felt creep onto your cheeks wasn’t as noticeable as it felt.  
You spent the better part of the next hour entranced with Sam. He was much different than the boy you remembered, but in the five years since you had seen him last, heartbreak had struck, and the melancholy that washed over his features when he mentioned Jessica made him look 17 again. You weren’t sure whether you wanted to bundle him up and keep him safe or help him arm himself against the monster that took his girl.  
When your waitress came over looking irritated, you realized the three of you had outstayed your welcome. Glancing at your watch you noticed that the time had flown by and you were going to be late for your interview if you didn’t leave in the next five minutes. You reached into your bag, and handed a set of keys to Dean along with a card with your cell phone number on it. You grabbed a second card and a pen asking, “What’s the best number to get ahold of you guys? I can call after I’m finished and maybe meet up with your, or we can head to my apartment.”  
Dean rattled off a couple sets of numbers as he and Sam stood. Once you were on your feet, Dean embraced you quickly. “Talk to you later, Y/N/N.”  
You walked over to hug Sam, too and his arms practically swallowed you up. “It was really good to see you. Really.” You stepped back, trying to catch Sam’s eye, but he was hiding behind his bangs.  
“You too, Sam. I hope this case is a bust, honestly. But we should hang out even if it is. Give Bobby a hard time for a couple days.” You weren’t sure where your burst of confidence came from, but you reached up on your tiptoes and tugged Sam’s shirt collar just a bit, placing a kiss on his cheek. “I’ll see you soon.”  
You spun and walked away, climbing into your Jeep, and missing Sam’s dumbfounded look. The song on the radio was just ending, some 90s afternoon jam. “So I should keep this to myself, And never let you know, I could fall in love with you.”


End file.
